The Last To Know
by Extrememusic22
Summary: Who will be the last to know that Dean Winchester is Bisexual? Starting in season 4, a series of one shots explaining each time every character realizes that Dean is Bi AF! Destiel, of course
1. The Old Magicians

**takes place during: Criss Angel is a Douche Bag**

"Does this look familiar to you?" Dean, or rather Federal Agent Ulrich, held out the probably magical Ten of Swords playing card.

The old magician, Vernon, raised a grey eyebrow, "Should it?"

Dean studied him carefully, "Well, I heard you used tarot cards in your act."

Vernon glanced at his friend Charlie and laughed, "My act? That was a long time ago."

While Dean and Vernon talked about who might have owned the card, Charlie paid attention. From the first glance Charlie knew this man was no FBI agent. But there was another secret, buried in there. Something about this guy's body language, his eyes, something. He was lying. Charlie couldn't quiet place it, until he heard Vernon say,

"Well, there was a guy on Bleeker street."

 _Of course!_ Charlie mentally scolded himself. He should've seen that from a mile away.

"Oh yeah," Charlie interjected, "He, he peddles that kind of specialty stuff."

"Did he have a problem with Vance?" Dean inquired. Finally, he was getting somewhere. Maybe this case could be wrapped up by tonight.

Vernon and Charlie were quick to supply more details, and Dean felt like he could breathe a sigh of relief. Finally, some simple answers.

Charlie had a twinkle in his eyes as he studied the man closer. "Ask for Chief." He added, noticing Vernon trying to contain his laughter.

"Chief," The 'agent' nodded, "Thank you."

As soon as he was gone, Vernon stopped holding back.

" _Chief!_ Ah, Charlie that's too good." Vernon chuckled.

"Serves the kid right," Charlie took a sip of his drink, "Thinking he can con the con artist. Please!"

"To be fair," Vernon held up a finger, "He's conning himself, too."

Charlie smiled, "I've heard of people repressing gay feelings, but this would be the first I've heard of someone not knowing they're not actually from the FBI."

Vernon rolled his eyes, "You know what I meant. I wonder what he wanted to know about that damn card that would make him get a fake badge. Pretty good quality, too."

Charlie just took another sip. "Who knows? Hey, maybe we did the kid a favor. Maybe Chief is the wakeup call he needs."

Vernon choked on laugher.


	2. The Siren Named Munroe

**takes place during Sex and Violence**

Dean slid into the passenger seat of actual FBI Agent Munroe's car. Munroe looked about 30, with a round face and full lips. His brown eyes looked Dean up and down quickly.

"She went inside just a few second ago."

Dean glanced at Munroe and gave a satisfied nod, "nice work."

Munroe leaned towards him, "Should we follow her in?"

It must have been the way they were sitting- or maybe the lighting. Yeah, it was the lighting that made Dean stare at Munroe's mouth. "No,no,no." Dean stammered, "I don't wanna tip her off. Let's just . . ." Dean mentally slapped himself, "Let's just wait and see who she comes out with."

Munroe's face twisted into a look of disbelief. Dean faced forward, and tried to think straight- literally.

"So what, she's drugging them?"

Dean swallowed, "It's kinda hard to explain, but I have my reasons and they're good ones, so you're just gonna have to trust me on 'em."

"Yeah, okay." Munroe shifted in his seat so his full torso faced Dean. "I trust you."

It was like a weight was lifted on Dean's shoulders. He couldn't look away any longer. "Thank you." He let himself study Monroe's face, half covered by shadow, "That's actually. . . nice to hear." Hesitantly, Dean reached into his pocket and brought out his flask. He needed a drink.

"So let's say she is drugging her vics. How's she pulling it off?" Munroe asked, innocently. Dean offered him the flask, which he took a drink from eagerly. Dean took back the flask, and drank again.

"She could be injecting them," Dean said, keeping his voice light, "or you know," Dean began blushing in a very un-Dean-like way, "passing the toxin through," Dean wanted to finish the whole flask right there, "physical contact."

"Or it could be saliva," Munroe began smiling, "You know, you really should've wiped the lid of that thing before you drank it, Dean."

Suddenly Dean's eyes widen, but at the same time he felt a rush of relief. That's what these weird feelings were. Munroe was the siren- he was just under a spell.

Munroe began to chuckle, "I knew you were going to be my target from the moment you and Sammy got into town. And I began thinking, who should I be to seduce Dean Winchester?" Munroe put his hand on the back of Dean's neck, and gently pulled his face closer. They were only inches apart. And Munroe smiled. "Siren's have a special gift. We know your hearts true desire." And suddenly, Munroe closed the space between them. They were kissing.

Dean internally screamed, and kicked, and panicked- he was _not_ gay. . . but, he was under the siren's spell. This wasn't real. And so Dean externally was . . . relaxed. And enjoying himself.

Munroe was the one to break away, breathlessly grinning. "You see, Dean? We should be together. We could be together."

Dean's mind was a jumble. "Yeah."

"It's just," Munroe licked his lips, "Sam. Bobby. Your father. They wouldn't understand. They'd be angry, and disgusted. Why can't they let you be happy, Dean? That's not very fair."

Dean glared, "Yeah."

Munroe grabbed Dean's collar, and leaned closer again, "They don't love you- the real you. Not like I can. In fact, you should probably get Sam and Bobby out of the way. So we can be together, forever."

And like that, Dean's mind was cleared. Everything made perfect sense. "Yeah," Dean nodded, "okay."

Munroe happily sat back, and started the car. It was always more fun when you could be your victim's first. Munroe knew that he had been Dean's first boy-kiss. And he certainly didn't plan to stop there.


	3. Chuck Shirley

**Hey guys! I really appreciate you taking the time to read this story! I would love to hear your thoughts and opinions, because I think my writing could use some work! Thanks** **J**

 **Takes place during The Monster at the End of This Book**

Chuck Shirley had been surprised before. On his 13th birthday he had entered his house only to find his mom, his cousin, and his neighbor sitting in the darkness, waiting with cake and three hastily wrapped presents (new shoes, gum, and socks. Exciting stuff). When he was a freshman in college, his girlfriend of three months knocked on his dorm room door and confessed that she finally realized she was a lesbian. The fact that she realized this moments after their first time, Chuck was sure, happened to be a coincidence.

But nothing had ever surprised Chuck as much as discovering the two crazy brothers he's been writing about were real. All of it was real. It blew his mind into tiny dust particles.

Chuck looked at them now, Sam and Dean, standing in the flesh in front of him. And although they'd never technically met before, Chuck could practically read their minds. He knew them, probably more than they knew themselves and a hell of a lot more than they knew each other. He began to pace, holding pages in his hands.

"So, you wrote another chapter?" Sam asked, watching Chuck walk back and forth.

Chuck explained the vision he had, involving Sam and Lilith and a bed. Dean seemed pissed- no, Chuck _knew_ he was pissed. The brothers left, and after an extremely long day Chuck collapsed on his couch. He would just rest for a little while. . .

 _Briiing. Briiiing. Briiiiiiiiing._

Reluctantly, Chuck opened his eyes. Great. Who could it be this time, Harry Potter or Tom Sawyer? He pulled himself up and answered the phone.

After locating the Toreador Motel (man, they should really fix those lights), Chuck made his way to the room number Sam told him, and knocked.

Sam pulled open the door, and Chuck raised an eyebrow.

"You wanted to see me?"

Sam stepped back, "Yeah." He let Chuck into the room and quickly shut the door. Chuck glanced around. Not exactly the classiest place he'd been to- but not the trashiest either.

"Thanks for coming," Sam said.

"Ah, sure," he responded, with a quick smile. God, this was so weird.

"Um…" Sam shifted his weight, "I was just wondering how much you know. About me."

"What do you mean?"

Sam hesitantly stepped forward, "Have you seen visions of me when I'm not with Dean?"

"Oh…" Chuck took a deep breath, "You want to know if I know about the demon's blood."

"You didn't tell Dean." Sam said quietly.

"I didn't even write it into the books." Chuck responded. Perhaps, deep down, he'd always felt that his characters were a little bit real. There were some things he just couldn't bring himself to reveal. Like Sam's blood-habit. Like Dean's thoughts. "You've got to know that's wrong."

"It scares the hell out of me," Sam confessed, since there was clearly no point of hiding. Chuck was in his head. "I mean, I feel it inside of me. I. . . I wish to God I could stop."

Chuck glanced at Sam. "You know, you and Dean are more alike than you think."

Sam looked up sharply, "What does that mean?"

"It's just. . ." Chuck drifted off. Publically sharing these boy's lives were one thing, but telling one the other's secret? That seemed too harsh. _Besides_ , Chuck thought to himself, _that's not the way the story goes_. "I thought saving the world was Dean's job? That's what the angels say, right?" Of course Chuck had to bring up the angels- right when he was trying to keep Dean's sexuality on the down low. _Stupid_.

"Dean's not. . . he's not Dean lately," Sam admitted, "Not since he got out of hell."

 _Not since he met Cas_ , Chuck thought.

"He needs help," said Sam, more confidently.

Chuck studied the younger brother carefully. He wasn't wrong- he just wasn't completely right, either. Maybe someday he'd understand. Maybe some chapter.


	4. The Trickster

**Thank you guys SO much for reading! :D Please feel free to leave comments and give me advice or just your opinions :)**

 **Takes place during** **Changing Channels**

The brothers were trapped in a goddamn sitcom, and if Dean heard one more laugh track he was going to _lose it_.

"How was that funny?!" Dean asked, ready to beat the crap out of the soon-to-be-dead studio audience, " _Vultures_."

Another laugh track. Suddenly, before Dean could pounce, the door burst open and there stood Castiel, clearly injured.

Dean was surprised, filled with a strange mix of worry and relief, "You okay?"

"I don't have much time," Cas said, urgently. Dean's stomach plunged as he studied Cas' injuries. They needed to get somewhere safe.

"What happened?" Sam asked.

"I got out," Cas explained.

"From where?" demanded Dean, getting real tired of all these stage-and-lights TV bullcrap. He wanted the real world back.

Cas quickly explained that he knew something was wrong- this supposed "trickster" was far too powerful. Sam and Dean didn't understand- and before they could Cas was flung up against the wall by a mysterious force.

The Trickster appeared in the doorway, to a chorus of applause from that seriously annoying audience. "Hello!" he said cheerfully, "thank you, thank you ladies!" he quickly blew a kiss to his invisible fans. Cas pulled himself up- but his mouth was covered in duct tape.

"Hi Castiel!" The Trickster gave a light wave in the angel's direction. Suddenly, Cas disappeared into a cloud of static. His grin grew wider, "Bye Castiel!"

Dean stepped forward, furious, "Where did you send him?!"

"Relax," the Trickster casually walked towards the brothers, paying special attention to Dean. A very important trait of a trickster is knowing yourself- your abilities, your limits. But an equally, if not more important, trait is the ability to know others. The Trickster could read Dean like the back of a cereal box (preferably Lucky Charms). Another, and perhaps the most well-known trait, was taking pleasure from others people's misery. And this Trickster knew exactly what to say to push Dean's buttons.

"He'll live..." he continued, staring at Dean, " _maybe_."

Dean exploded, "All right, you know what? I'm done with the monkey dance, okay?! We get it."

Sam glanced at his brother, feeling slightly unsure if confronting the monster that just flicked a literal angel away like he was a gnat was a smart idea. But obviously, Dean was already going for it.

"Get what, hot shot?" The Trickster folded his arms, smirking. This oughta be good.

"Playing our roles, right? That's your game." Said Dean, upset.

"That's half the game."

"What's the other half?" Sam asked, still sticking to his original plan of trying to reason with this supposed Trickster. Maybe he could still be helpful.

"Play your roles out there," God, did he have to spell it out for them?! For the brightest hunters of their age, the Winchesters could be real dumbasses sometimes.

Dean huffed, "What is that supposed to mean?"

The Trickster rolled his eyes, "Oh, relax Dean, I'm not talking about your role as a womanizing pervert, okay? Play it, don't play it- I don't care. I'm talking about, well, you know. Sam starring as Lucifer. Dean starring as Michael. Your celebrity death match."

"You want us to say _yes_ to those sons of bitches?!" Sam asked, incredulously. "We do that, and the world will end!"

Sam and the Trickster kept talking, but Dean was thinking. What the hell was this- this _whatever_ talking about? Dean loved women, nad if that made him certain things, then so be it. He wasn't playing anything.

"Which side are you on, heaven or hell?" Dean demanded to know.

He smirked, "Honestly, from one trickster to another- I'm not on either side."

Dean didn't know what this monster was talking about, but it really pissed him off, "Oh, you're somebody's bitch."

The Trickster's smile vanished, he grabbed Dean by the collar and slammed him against the wall. At the same time Sam was pushed back, and the Trickster spoke low so the younger brother _and_ the studio audience couldn't hear.

"Listen to me, you arrogant dick," he said, getting in Dean's face. "You didn't know that your brother was going dark side, you don't know why cute little Castiel is risking his cute little ass for you- hell, you don't know your own freaking self- so don't you ever assume you know _anything_ about me." The Trickster stepped back from Dean, who was still stuck on the wall, so he could now include Sam who was trapped on the floor a few feet away.

"Here's what's gonna happen," He announced, clasping his hands together, "You're gonna suck it up, accept your responsibilities, and play the roles that fate has chosen for you." He glared at Dean, "even if that means you have to change yourself. Its destiny, deal with it. Understood?"

"And if we don't?" Sam asked, fighting against the invisible force that was keeping him down.

The Trickster smiled. He felt pretty good about whipping Dean into shape. The oldest Winchester's green eyes were glued to the floor. He was clearly trying very hard to not think. If only Sam had secret gay feelings for someone. The Trickster walked over to the younger brother, and looked down. He wasn't too bad on the eyes. Hell, maybe one day he could have secret gay feelings for him. The thought made his twisted smile widen.

"Then you'll stay here in TV land forever. Three hundred channels and, uh, nothing's on."


	5. Jo

**Thank you guys SO MUCH for reading and your reviews! :D Sorry I haven't updated more- but I'm going to try and be a lot more consistent! My homework load has been crazy :)**

 ** _Takes place during "Abandon All Hope…."_**

Castiel watched as Crowley pulled the extremely uncomfortable human man in for a kiss. Cas' insides twisted. It wasn't like he hadn't seen physical affections before, but it was definitely the first time he'd really. . . thought about it. About what it must be like.

"Cas?" Dean's voice spoke in his ear, as he suddenly remembered that he was holding a phone. Right. He was an angel on a mission. With the Winchesters. Cas made sure to keep his voice steady as he answered back,

"Got him."

They had the Colt, they had a (admittedly sketchy) plan, and they had one more night at Bobby's house. Dean and Sam clinked their beers together, and took a drink. They would fight this devil the way they did best- together.

Dean looked at his little brother, and didn't know what to say. Or maybe he did, but couldn't figure out how. So he smirked, and leaned back in his chair.

"This is a stupid friggin' idea."

As he spoke, his eyes drifted towards Helen, Jo, and Cas- obviously in the middle of some ridiculous drinking game. Sam saw his look, and turned around in his chair to see for himself.

Jo glanced up when she noticed Cas' posture straighten. She saw the brothers both looking them over, but unlike Sam, Dean didn't seem amused. He seemed peaceful. His wide green eyes were fixed directly at Cas. She could tell that the angel was staring back with an un-earthly amount of intensity.

Jo had watched enough day time dramas to know what was going on here.

Later that night, it took Dean longer than Jo thought to give her the good old 'last night on earth' speech. And maybe, a month ago, that would've worked. Dean was strong, and (sometimes) funny. He had great sandy hair, and honestly beautiful eyes. If numbers were any indication he was probably fantastic in bed- and more importantly, he was her friend.

Jo leaned in towards him, their mouths inches apart. She stared into his deep green eyes, and she didn't see lust. She saw desperation. Dean didn't want her- he needed her. He needed to be with somebody, and obviously he was too blind to see who that somebody was supposed to be.

Jo wouldn't mind being a one night stand. But she would never be a second choice.

"If this is our last night on Earth," Jo raised her eyes to meet his, "then I'm gonna spend it with a little thing I call self-respect."


End file.
